Cytotoxic and Antiviral Compounds from Bryophytes and Inedible Fungi

Journal of Pre-Clinical and Clinical Research, 2013, Vol 7, No 2, 73-85 ORIGINAL ARTICLE www.jpccr.eu Cytotoxic and Antiviral Compounds from Bryophytes and Inedible Fungi Yoshinori Asakawa1, Agnieszka Ludwiczuk1,2, Toshihiro Hashimoto1 1 Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, Japan 2 Department of Pharmacognosy with Medicinal Plants Laboratory, Medical University of Lublin, Poland Asakawa Y, Ludwiczuk A, Hashimoto T. Cytotoxic and Antiviral Compounds from Bryophytes and Inedible Fungi. J Pre-Clin Clin Res. 2013; 7(2): 73–85. Abstract Over several hundred new compounds have been isolated from the bryophytes and more than 40 new carbon skeletal terpenoids and aromatic compounds found in this class. Most of liverworts elaborate characteristic odiferous, pungent and bitter tasting compounds many of which show, antimicrobial, antifungal, antiviral, allergenic contact dermatitis, cytotoxic, insecticidal, anti-HIV, superoxide anion radical release, plant growth regulatory, neurotrophic, NO production inhibitory, muscle relaxing, antiobesity, piscicidal and nematocidal activity. Several inedible mushrooms produce spider female pheromones, strong antioxidant, or cytotoxic compounds. The present paper concerns with the isolation of terpenoids, aromatic compounds and acetogenins from several bryophytes and inedible fungi and their cytotoxic and antiviral activity. Key words bryophytes, inedible fungi, terpenoids, bis-bibenzyls; cytotoxicity, antiviral activity 1. CHEMIcaL CONSTITUENTS OF BRYOPHYTES 1.1 Introduction The bryophytes are found everywhere in the world except in the sea. They grow on wet soil or rock, the trunk of trees, in lake, river and even in Antarctic island. The bryophytes are placed taxonomically between algae (Fig. 1) and pteridophytes (Fig. 2); there are approximately 24,000 species in the world. They are further divided into three phyla, Bryophyta (mosses 14,000 species, Fig. 3), Marchantiophyta (liverworts 6,000 species, Fig. 4a, 4b) and Anthocerotophyta (hornworts 300 species, Fig. 5). Although they are considered to be the oldest terrestrial plants, no strong scientific evidence for this has appeared in literatures. This hypothesis is mainly based on the resemblance of the present-day liverworts to the first land plant fossils, the spores of which date back almost 500 million years. Among the bryophytes almost Figure 2. Fern Figure 1. Green algae Figure 3. Moss Address for correspondence: Yoshinori Asakawa, Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, Japan all liverworts possess beautiful cellular oil bodies (Fig. 6) e-mail: [email protected] which are peculiar membrane-bound cell organelles that Received: 01 August 2013; accepted: 30 December 2013 consist of ethereal terpenoids and aromatic oils suspended 74 Journal of Pre-Clinical and Clinical Research, 2013, Vol 7, No 2 Yoshinori Asakawa, Agnieszka Ludwiczuk, Toshihiro Hashimoto. Cytotoxic and Antiviral Compounds from Bryophytes and Inedible Fungi Figure 4a. Thalloid liverwort. Figure 5. Hornwort Figure 4b. Stem-leafy liverwort. Figure 6. Oil bodies of the liverwort Frullania vethii in carbohydrates- or protein-rich matrix, while the other 1.2 Bio- and Chemical Diversity of Bryophytes two phyla do not. These oil bodies are very important 1.2.1 Biodiversity of bryophytes biological marker for the taxonomy in the Marchantiophyta The Marchantiophyta includes two subclasses, the [1–8]. Phytochemistry of bryophytes has been neglected for Jungermanniidae and Marchantiidae, and six orders, 49 a long time because they are morphologically very small families, 130 genera and 6,000 species. Still many new species and difficult to collect a large amount as pure sample, their have been recorded in the literatures. The southern hemisphere identification is also very difficult even under the microscope. together with tropic region is characterized by extraordinarily They are considered to be nutritionally useless to humans. high liverwort diversity [14]. This area has more endemic In fact, nothing references concerning use as foods for liverwort species than the northern hemisphere. As seen in humans have been seen. However, a number of bryophytes, Fig. 7, there are 54 endemic genera in southern hemispheric especially, mosses have been widely used as medicinal plants countries, such as New Zealand and Argentina [15]. In in China, to cure burns, bruises, external wounds, snake Asia including Japan, relatively large number of endemic bite, pulmonary tuberculosis, neurasthenia, fractures, genera (21) also has been recorded, however, South Africa, convulsions, scald, uropathy, pneumonia, neurasthenia etc. Madagascar and both North America and Europe are very as shown in Table 1 [9–11]. poor regions of endemic liverworts. The richness of endemic Many species of liverworts show characteristic fragrant odors genera of bryophytes in southern hemisphere suggests that the and an intense pungent, sweet or bitter taste. Generally, bryophytes might originate from the past Antarctic islands bryophytes are not damaged by bacteria and fungi, insect since 350 – 400 million years ago and developed to the northern larvae and adults, snails, slugs and other small mammals. hemisphere with a long range evolutionary process. In Japan, Furthermore, some liverworts cause intense allergenic Yaku Island is the most important place to watch many species contact dermatitis and allelopathy. Although liverworts of the Marchantiophyta. In the southern hemisphere, New possess such pharmacologically interesting substances, their Zealand is the most charming country to see many different isolation and the structural elucidation were neglected for species of the Marchantiophyta which are totally different almost one century. from those found in the northern Asia, including Japan. The paper concerns with the cytotoxic and antiviral activity In the tropical regions, such as south-east Asia, Borneo, of terpenoids, aromatic compounds and acetogenins from Sumatra and Papua New Guinea and Colombia, Ecuador and bryophytes [2–4, 8, 12, 13]. Venezuela, there are rain forests where so many liverworts Journal of Pre-Clinical and Clinical Research, 2013, Vol 7, No 2 75 Yoshinori Asakawa, Agnieszka Ludwiczuk, Toshihiro Hashimoto. Cytotoxic and Antiviral Compounds from Bryophytes and Inedible Fungi Table 1. Medicinal bryophytes and their biological activity and effects Musci: Biological activity and effects Bryum argenteum Antidotal, antipyretic, antirhinitic activity; for bacteriosis Cratoneuron filicinum For malum cordis (heart disease) Ditrichum pallidum For convulsions, particularly in infants Fissidens japonicum Diuretic activity; for growth of hair, burns, and choloplania (jaundice, icterus) For hemostatis, pulmonary tuberculosis, vomitus cruentus (hematemesis), bruises, and athlete’s foot dermatophytosis (dermatomycosis, Funaria hygrometrica dermomycosis) Haplocladium catillatum Antidotal, and antipyretic activity; for adenopharyngitis, pharyngitis, uropathy, mastitis, erysipelas (rose), pneumonia, urocystitis, and tympanitis Leptodictyum riparium Antipyretic; for choloplania, and uropathy Mnium cuspidatum For hematostasis and nosebleed Oreas martiana For anodyne (pain), hemostasis, external wounds, epilepsy, menorrhagia, and neurasthenia (nervosism, nervous exhaustion) Philonotis fontana Antipyretic, antidotal activity; for adenopharyngitis Plagiopus oederi As a sedative; for epilepsy, apoplexy, and cardiopathy Polytrichum species Diuretic activity; for hair growth Polytrichum commune Antipyretic, and antidotal; for hemostasis, cuts, bleeding from gingivae, hematemesis, and pulmonary tuberculosis Rhodobryum giganteum Antipyretic, diuretic, and antihypertensive; for sedation, neurasthenia, psychosis, cuts, cardiopathy, and expansion of heart blood vessels Rhodobryum roseum As a sedative; for neurasthenia, and cardiopathy Taxiphyllum taxirameum Antiphlogistic; for hemostasis, and external wounds Weissia viridula Antipyretic, and antidotal; for rhinitis Hepaticae: Biological activity and effects Antimicrobial, antifungal, antipyretic, antidotal activity; used to cure cuts, burns, scalds, fractures, swollen tissue, poisonous snake bites, and Conocephalum conicum gallstones Frullania tamarisci Antiseptic activity Marchantia polymorpha Antipyretic, antihepatic, antidotal, diuretic activity; used to cure cuts, fractures, poisonous snake bites, burns, scalds, and open wounds Reboulia hemisphaerica For blotches, hemostasis, external wounds, and bruises bryophytes and their structures were elucidated [2, 3, 4]. Most of compounds found in liverworts are composed of lipophilic mono-, sesqui- and diterpenoids and aromatic compounds, such as typical bibenzyls and bis-bibenzyls. The most characteristic chemical phenomenon of liverworts is that most of sesqui- and diterpenoids are enantiomers of those found in higher plants although there are a few exceptions such as germacrane- and guaiane-type sesquiterpenoids. It is very noteworthy that the different species of the same genera, like Frullania tamarisci and F. dilatata (Frullaniaceae) each produces different sesquiterpene lactone enatiomers. Some liverworts, such as Lepidozia species (Lepidoziaceae), biosynthesize both enantiomers. Flavonoids, fatty acids and phytosterols are ubiquitous components in bryophytes and have been isolated Figure 7. The distribution of endemic liverwort genera from or detected both in liverworts and mosses. However, the presence of nitrogen

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